1,8-Naphthalimide Synthon in Silver Coordination Chemistry:  Control of Supramolecular Arrangement

• Published in: Crystal growth & design Vol. 6; no. 12; pp. 2758 - 2768
• Main Authors: Reger, Daniel L, Semeniuc, Radu F, Elgin, J. Derek, Rassolov, Vitaly, Smith, Mark D
• Format: Journal Article
• Language: English
• Published: Washington,DC American Chemical Society 06-12-2006
• Subjects: Condensed matter: structure, mechanical and thermal properties; Cross-disciplinary physics: materials science; rheology; Exact sciences and technology; Growth from solutions; Materials science; Methods of crystal growth; physics of crystal growth; Organic compounds; Physics; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Weak interactions; Stacking sequence; Tetragonal lattices; Organometallic compounds; Crystallization; Experimental study; Monoclinic lattices; Imides; Organic solution; Triclinic lattices; Hydrogen bonds; Supramolecular structure; Silver complexes; Crystal growth from solutions; Crystal structure; Synthon
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/cg060460p

The reaction of N-[2,2-bis(pyrazolyl)ethane]-1,8-naphthalimide (L1) and N-[2,2-bis(3,5-dimethylpyrazolyl)ethane]-1,8-naphthalimide (L2) with silver tetrafluoroborate produced two new compounds, formulated on the basis of elemental figures and ESI/MS+ experiments as [Ag(L1)2](BF4) and [Ag(L2)2](BF4), respectively. Crystallization of these two compounds resulted in the formation of two pseudopolymorphs in each case; the structures of all four have been determined by X-ray crystallography. The common feature of all four structures is the directional π−π stacking of the naphthalimide groups, with the dipole vectors oriented at 180° antiparallel. The crystal packing is also influenced by several other noncovalent interactions, such as the pyrazolyl embrace, C−H···π interactions, and weak C−H···O hydrogen bonds.